Process for recovering a mixture comprising a (thio)phosphoric acid derivative

Abstract

Provided herein is a use of a high-boiling solvent in a mixture comprising a (thio)phosphoric acid derivative and a process including the addition of a high-boiling solvent to a mixture comprising a (thio)phosphoric acid derivative to recover the (thio)phosphoric acid from the mixture by an evaporation process.

The invention claimed is: 
     
       1. A method of using at least one high-boiling solvent having a boiling point of at least 130° C., in a mixture comprising at least one (thio)phosphoric acid derivative and at least one volatile component, for preventing decomposition or solids formation of the at least one (thio)phosphoric acid derivative in an evaporation process, wherein said evaporation process comprises:
 separating the at least one (thio)phosphoric acid derivative from the at least one volatile component, wherein the at least one volatile component is selected from the group consisting of liquid paraffinic, cycloparaffinic, and/or aromatic hydrocarbons, liquid halocarbons and halohydrocarbons, ethers, and esters; and 
 recovering as a bottom product a first mixture (1) comprising components: 
 (1a) the at least one (thio)phosphoric acid derivative; and 
 (1b) the at least one high-boiling solvent, wherein the at least one (thio)phosphoric acid derivative is selected from the group consisting of: (thio)phosphoric acid triamides according to general formula (I) and (thio)phosphoric acid ester amides according to general formula (IIa) or (IIb); 
 wherein general formula (I) is 
 
       
         
           
           
               
               
           
         
         wherein 
         X 1  is O or S; 
         R 1  is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; 
         R 2  is H, C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; or 
         R 1  and R 2  together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of N, O, and S; and 
         R 3 , R 4 , R 5 , and R 6  are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl; 
         and wherein general formula (IIa) is 
       
       
         
           
           
               
               
           
         
         wherein 
         X 2  is O or S; 
         R 7  is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; and 
         R 8 , R 9 , R 10 , and R 11  are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl; 
         and wherein general formula (IIb) is 
       
       
         
           
           
               
               
           
         
         wherein 
         X 3  is O or S; 
         R 12  is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; 
         R 15  is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; and 
         R 13  and R 14  are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl, and 
         wherein the at least one high-boiling solvent is hydrophilic. 
       
     
     
       2. The method according to  claim 1 , wherein the at least one volatile component comprises at least one solvent having a boiling point of at least 30° C. lower than the boiling point of the at least one high-boiling solvent. 
     
     
       3. The method according to  claim 1 , wherein the at least one high-boiling solvent is further used as a formulation agent for the at least one (thio)phosphoric acid derivative in the recovered first mixture (1). 
     
     
       4. A process for recovering at least one (thio)phosphoric acid derivative from a first mixture comprising the at least one (thio)phosphoric acid derivative and at least one solvent, wherein the process comprises:
 adding at least one high-boiling solvent having a boiling point of at least 130° C. to the first mixture so as to form a second mixture (2) comprising components: 
 (2a) the at least one (thio)phosphoric acid derivative; 
 (2b) the at least one high-boiling solvent; and 
 (2c) the at least one solvent, the at least one solvent having a boiling point that is at least 30° C. lower than the boiling point of the at least one high-boiling solvent to be and is selected from liquid paraffinic, cycloparaffinic, and/or aromatic hydrocarbons, liquid halocarbons and halohydrocarbons, ethers, and esters; and 
 and separating a third mixture (1) from said second mixture (2), wherein said third mixture (1) comprises components: 
 (1a) the at least one (thio)phosphoric acid derivative; and 
 (1b) the at least one high-boiling solvent; 
 by evaporating the at least one solvent component (2c) of the second mixture (2) and collecting the third mixture (1) as a bottom product, wherein the at least one (thio)phosphoric acid derivative is selected from the group consisting of: (thio)phosphoric acid triamides according to general formula (I) and (thio)phosphoric acid ester amides according to general formula (IIa) or (IIb); 
 wherein general formula (I) is 
 
       
         
           
           
               
               
           
         
         wherein 
         X 1  is O or S; 
         R 1  is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; 
         R 2  is H, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; or 
         R 1  and R 2  together with the nitrogen atom linking them define a 5- or 6-membered saturated or unsaturated heterocyclic radical, which optionally comprises 1 or 2 further heteroatoms selected from the group consisting of N, O, and S; and 
         R 3 , R 4 , R 5 , and R 6  are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl; 
         and wherein general formula (IIa) is 
       
       
         
           
           
               
               
           
         
         wherein 
         X 2  is O or S; 
         R 7  is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; and 
         R 8 , R 9 , R 10 , and R 11  are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl; 
         and wherein general formula (IIb) is 
       
       
         
           
           
               
               
           
         
         wherein 
         X 3  is O or S; 
         R 12  is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; 
         R 15  is C 1 -C 20 -alkyl, C 3 -C 20 -cycloalkyl, C 6 -C 20 -aryl, C 6 -C 20 -aryl-C 1 -C 4 -alkyl, or C 1 -C 6 -(di)alkylaminocarbonyl; and 
         R 13  and R 14  are independently of each other selected from the group consisting of H and C 1 -C 4 -alkyl, and 
         wherein the at least one high-boiling solvent is hydrophilic. 
       
     
     
       5. The process according to  claim 4 , wherein
 evaporating the at least one solvent component (2c) of the second mixture (2) and collecting the third mixture (1) as the bottom product is performed by: 
 (i) continuously introducing a stream of the second mixture (2) into at least one thin film evaporator operating at a temperature of from 40° C. to 160° C. and at a pressure of from 5 mbar to 300 mbar (0.5 kPa to 30 kPa); and 
 (ii) continuously collecting the bottom product. 
 
     
     
       6. The process according to  claim 4 , wherein the first mixture further comprises at least one HCl scavenger having a boiling point of at least 30° C. lower than the boiling point of the at least one high-boiling solvent.